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A Chlorine-Bearing Asymmetric Center as a Stereocontrol Element in a Short Formal Synthesis of Steviol. 含氯不对称中心在甜菊糖短形式合成中的立体控制元件。
IF 2.3 4区 化学
Synthesis-Stuttgart Pub Date : 2025-09-04 DOI: 10.1055/a-2695-8576
Sharon E Michalak, Christopher D Vanderwal
{"title":"A Chlorine-Bearing Asymmetric Center as a Stereocontrol Element in a Short Formal Synthesis of Steviol.","authors":"Sharon E Michalak, Christopher D Vanderwal","doi":"10.1055/a-2695-8576","DOIUrl":"10.1055/a-2695-8576","url":null,"abstract":"<p><p>Steviol is one of myriad polycyclic terpenoids bearing oxygenation on the axially disposed C19 carbon. The presence of this C19 alcohol renders the C4 quaternary carbon stereogenic, issuing a challenge for stereoselective synthesis. Here we show that a suitably disposed chlorine atom at C2, coupled with the correct diastereomer of terminal epoxide that initiates cationic bicyclization, leads to the desired stereochemical outcome. Subsequently, the anisole terminating group undergoes Birch reduction that simultaneously reduces the C-Cl bond, removing the transient \"auxiliary\" and completing a short, highly stereoselective formal synthesis of steviol. This work provides another example of the power of removable C-X bonds for stereocontrolled synthesis.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" ","pages":""},"PeriodicalIF":2.3,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12456424/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145139288","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization. Nugent-RajanBabu还原环氧化物环化过程中意想不到的区域化学控制。
IF 2.3 4区 化学
Synthesis-Stuttgart Pub Date : 2025-08-08 DOI: 10.1055/a-2680-2368
Nantamon Supantanapong, Scott W Niman, Christopher D Vanderwal
{"title":"Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization.","authors":"Nantamon Supantanapong, Scott W Niman, Christopher D Vanderwal","doi":"10.1055/a-2680-2368","DOIUrl":"10.1055/a-2680-2368","url":null,"abstract":"<p><p>The Nugent-RajanBabu reductive epoxide cyclization has become a mainstay of alternative methods to accomplish classical, biomimetic, cationic polyene cyclizations. In most cases, the regiochemical control for the formation of decalins and perhydrophenanthrenes is exquisite, mirroring that obtained in cationic reactions, to the point where the 6-<i>endo</i> reactivity is anticipated even in the face of potential 5-<i>exo</i> processes. In our studies toward complex, polyoxygenated terpenoid natural products, we had cause to evaluate the reactions of α-alkoxy epoxides in these types of reactions, and we were surprised to uncover a means to control 6-<i>endo</i> vs 5-<i>exo</i> reactions based on the size of the protecting group on the α-oxygen. This knowledge opens up the possibility of rapid syntheses of highly oxygenated cyclopentane systems, in addition to the expected decalin scaffolds.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" ","pages":""},"PeriodicalIF":2.3,"publicationDate":"2025-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12456417/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145139261","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing. 利用吡咯-吡啶分子编辑实现了康帕那定A的简洁全合成。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2024-01-01 Epub Date: 2023-07-03 DOI: 10.1055/a-2107-5159
Brandon S Martin, Donghui Ma, Takeru Saito, Katelyn S Gallagher, Mingji Dai
{"title":"Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.","authors":"Brandon S Martin, Donghui Ma, Takeru Saito, Katelyn S Gallagher, Mingji Dai","doi":"10.1055/a-2107-5159","DOIUrl":"10.1055/a-2107-5159","url":null,"abstract":"<p><p><i>Lycopodium</i> alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management. Herein, we reported a concise synthesis of complanadine A using a pyrrole-to-pyridine molecular editing strategy. The use of a nucleophilic pyrrole as the precursor of the desired pyridine enabled an efficient and one-pot construction of the tetracyclic core skeleton of complanadine A and lycodine. The pyrrole group was then converted to a 3-chloropyridine via the Ciamician-Dennstedt one carbon ring expansion. A subsequent C-H arylation between the 3-chloropyridine and a pyridine <i>N</i>-oxide formed the unsymmetrical dimer, which was then advanced to complanadine A. Overall, from a readily available known compound, total synthesis of complanadine A was achieved in 11 steps. The pyrrole-to-pyridine molecular editing strategy enabled us to significantly enhance the overall synthetic efficiency. Additionally, as demonstrated by a Suzuki-Miyaura cross coupling, the 3-chloropyridine product from the Ciamician-Dennstedt rearrangement is amenable for further derivatization, offering an opportunity for simplified analog synthesis.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"8 1","pages":"107-117"},"PeriodicalIF":2.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11636943/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89430381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
SYNFORM ISSUE 2023/12 Synform issue 2023/12
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/s-0040-1720617
Matteo Zanda
{"title":"SYNFORM ISSUE 2023/12","authors":"Matteo Zanda","doi":"10.1055/s-0040-1720617","DOIUrl":"https://doi.org/10.1055/s-0040-1720617","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"25 9","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134992841","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization 碱基催化环化2-氧-2-(氨基)乙二硫酸酯合成2,4-和2,5-二取代1,3-噻唑的区域选择性
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/a-2210-6357
Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva
{"title":"Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization","authors":"Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva","doi":"10.1055/a-2210-6357","DOIUrl":"https://doi.org/10.1055/a-2210-6357","url":null,"abstract":"We herein report efficient methods for synthesis of 2,4- and 2,5-disubstituted-1,3-thiazoles 3(a-i) and 5(a-k) by the cyclization of 2-oxo-2-(amino)ethanedithioates with TosMIC and α-haloketones in high yields. The structures 3a and 5a were confirmed based on X-ray crystallographic studies. In addition, investigation of ground state geometry, electronic and molecular structural properties, FMOs, global reactivity descriptors, MEP and NCI analyses predicted to access the information related to the stability, reactivity, and strength of the interactions present in the molecules by quantum chemical calculations. Further, the potency of derivatives tested against the SARS-Cov2 receptor (PDB ID: 7mc6) via molecular docking approach with binding scores of –6.0 to –8.4 kcal/mol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"38 2","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134993136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs 5-(三烷基)硅基戊-1-烯-4-炔-3-酮与肼的反应:合成含唑基发光物质的原始途径
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-13 DOI: 10.1055/s-0043-1763601
Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova
{"title":"Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs","authors":"Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova","doi":"10.1055/s-0043-1763601","DOIUrl":"https://doi.org/10.1055/s-0043-1763601","url":null,"abstract":"Abstract On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"40 16","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136282055","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of All Regioisomers of 2-Aryl Azaindole-3-acetic Acid Derivatives 2-芳基氮唑-3-乙酸衍生物所有区域异构体的合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/a-2206-5900
Taewook Kim, Ju Hyeon Park, Cheol Jeong, Eunjoon Park, Jong Mu Kim, You-Jin Kim, Jung-Nyoung Heo, Cheol-Hong Cheon
{"title":"Synthesis of All Regioisomers of 2-Aryl Azaindole-3-acetic Acid Derivatives","authors":"Taewook Kim, Ju Hyeon Park, Cheol Jeong, Eunjoon Park, Jong Mu Kim, You-Jin Kim, Jung-Nyoung Heo, Cheol-Hong Cheon","doi":"10.1055/a-2206-5900","DOIUrl":"https://doi.org/10.1055/a-2206-5900","url":null,"abstract":"A novel protocol was developed for synthesizing 2-aryl substituted azaindole-3-acetic acid derivatives from 2-aminoazacinnamic acid derivatives and aryl aldehydes through an imino-Stetter reaction. Condensation of 2-aminoazacinnamic acid derivatives with aldehydes forms the corresponding aldimines, which are then treated with cyanide to yield the desired 2-aryl substituted azaindole-3-acetic acid derivatives. Notably, this protocol could be employed for the synthesis of all regioisomers of azaindole-3-acetic acid derivatives by using the appropriate azacinnamic acid derivatives.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135392120","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A 7A型肺炎链球菌荚膜多糖六糖重复单元的快速合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/s-0040-1720095
Samim Sahaji, Pradip Shit, Anup Kumar Misra, Swapan Kumar Jana
{"title":"Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A","authors":"Samim Sahaji, Pradip Shit, Anup Kumar Misra, Swapan Kumar Jana","doi":"10.1055/s-0040-1720095","DOIUrl":"https://doi.org/10.1055/s-0040-1720095","url":null,"abstract":"Abstract The hexasaccharide repeating unit corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 7A has been synthesized in good yield using [3+2+1] block synthetic strategy. The synthetic strategy involved a number of challenging stereoselective glycosylation steps, which include β-selective glycosylation of l-rhamnosyl thioglycoside donor, α-selective glycosylations of 2-azido-2-deoxy-d-glucopyranosyl thioglycoside donor and d-galactopyranosyl donor together with the formation of β-glycoside of d-galactosamine moiety and α-glycoside of l-rhamnosyl moiety. Suitably functionalized thioglycosides have been used as glycosyl donors and a combination of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf­) has been used as glycosylation promoter.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" 6","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135340663","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Ser-Ala-Ala Cyclic Desmosine Ser-Ala-Ala环氨基葡萄糖的合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-07 DOI: 10.1055/a-2205-7105
Shogo Satoh, Daria Baut, Moena Hirao, Daisuke Watanabe, Rina Suzuki, Toyonori Usuki
{"title":"Synthesis of Ser-Ala-Ala Cyclic Desmosine","authors":"Shogo Satoh, Daria Baut, Moena Hirao, Daisuke Watanabe, Rina Suzuki, Toyonori Usuki","doi":"10.1055/a-2205-7105","DOIUrl":"https://doi.org/10.1055/a-2205-7105","url":null,"abstract":"Elastin is present in the extracellular matrix of various tissues, most abundantly in the aorta and major vascular vessels, and is formed by self-assembly followed by concomitant crosslinkers of tropoelastin, an elastin precursor. Desmosine is a pyridinium-based tetrafunctional amino acid that serves as an important crosslinker to bind the polymeric chains of peptides in the 3D network of elastin. Despite its significance, the detailed structure of elastin has not been elucidated. In this work, we report the synthesis of a cyclic desmosine peptide designed to mimic elastin, which could serve as a compound for mass spectrometric analysis to elucidate crosslinking structures. The synthesis involved stepwise and regioselective palladium-catalyzed cross-couplings, and inter- and intramolecular condensations.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"18 3","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135539780","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total Synthesis of the Pyrrole Alkaloids Strychnuxinal and Strychnuxin 吡咯类生物碱士的宁和士的宁的全合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-07 DOI: 10.1055/s-0043-1763603
Keith P. Reber, Neechi F. Okwor, Priyansh D. Gujarati
{"title":"Total Synthesis of the Pyrrole Alkaloids Strychnuxinal and Strychnuxin","authors":"Keith P. Reber, Neechi F. Okwor, Priyansh D. Gujarati","doi":"10.1055/s-0043-1763603","DOIUrl":"https://doi.org/10.1055/s-0043-1763603","url":null,"abstract":"Abstract The first asymmetric total syntheses of the fused-pyrrole alkaloids strychnuxinal and strychnuxin have been achieved in 6 and 7 steps, respectively, starting from commercially available (±)-4-chlorostyrene oxide. Key steps in the synthetic route include a regioselective epoxide opening, a reductive etherification sequence to form the central 1,4-oxazine ring, and a late-stage phenol synthesis using a mild palladium-catalyzed coupling reaction. Notably, the optimized synthetic sequence presented avoids the use of traditional protecting groups. Total synthesis of these two structurally related natural products confirmed both their constitution (via NMR and X-ray crystallography) and their absolute configuration (via optical rotation).","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"39 3","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135432137","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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